[Uncover the secrets of Estonia]

5 Legends of Tallinn Old Town (and where to find them)

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Did you now that Tallinn Old Town is absolutely teeming with myths and legends?

You didn’t?

In that case, prepare to have the fires of your imagination stoked as we uncover the best kept secrets in the entire city. Despite the sheer density of these myths and legends, they remain notoriously well-hidden; available only to those who know where to look.

Hidden Tallinn has unearthed over a dozen of these stories over the years but which ones would we recommend to new visitors? Below is a beginners’ list of five legends of Tallinn Old Town complete with mapped links to help you find them. So without further ado, let’s delve into the fascinating world of Tallinn legends.

1) The Devil’s Wedding

First of all, we’re going straight for ‘number one’. This is the most famous tale of Old Town mythology.

On a cold winters night in medieval Tallinn, a strange cloaked figure knocked on the door of Rataskaevu 16 and hired the top floor room for a thunderousparty. He would pay handsomely on the condition that no-one would eavesdrop on the festivities.

Upon hearing the blasting music and raucous laughter, the owner became consumed by curiosity. After climbing the stairs, he defied his guest and peered in through the window. Instantly he fell back to the floor, recoiling in shock at what he saw.

Tallinn legend states that on that fateful winters night the owner had witnessed the Devil’s Wedding.

Today, the room itself has been sealed off to the outside world and in place of the frame and glass, a window has been painted to conceal the secrets hidden within those walls. Even today, guests of the hotel complain of strange clawing sounds emanating from this room.

2) The Danish King’s Garden

It may seem strange, but there is indeed a monument to a Danish King and an implausible miracle in the heart of the Old Town.

In 1215, the Danish King Valdemar II invaded Tallinn. Despite an early victory the Estonians fought back bravely and drove his forces all the way back to the brink of defeat. In his most desperate hour, the King fell to his knees and prayed to the heavens for some respite from this onslaught.

At that moment, a piece of fabric floated down from the clouds, landing at the Kings feet. Buoyed by this clear miracle, the Danish army fought back, over-turned the Estonian advantage and won this legendary battle.

What was so special about this piece of material you ask? Well, depicted on this heavenly fabric was a white cross laying on a red background. Immediately, the King adopted this as the official flag of Denmark where it still stands today – the longest serving national flag in the world.

The Danish King’s Garden was built on the spot where this symbolic fabric had landed.

3) The only Execution carried out in the Old Town

This story is so well hidden that many people stand on the spot of this execution every day, totally unaware of the gruesome events that took place.

In the late 1600s an angry priest threw a tankard full of warm beer at a barmaid, cracking her skull and killing her. Incensed with rage, the rabble of onlookers dragged the priest outside and demanded permission from the town hall to deliver swift, instant justice. Executions were usually enacted outside of the Old Town but such was the aggression of the mob, the priest was killed then and there.

Today a stone “L” marks the spot where the priest was executed – right in the corner of the Old Town Square, outside the old pharmacy. Make sure you time your visit right because the “L” is only visible in winter. In the summer it is concealed by the wooden restaurant terraces.

4) The Eye of the Needle

For a condemned criminal in medieval Tallinn, the odds of survival were pretty low. Once a death sentence was passed the victim would be paraded around the Old Town Square and lead down Harju Street to be executed outside of the Old Town.

Tallinn myth said that if a criminal could repent his sins by the time he was taken on his final walk then divine revelation and would allow him to slip away to safety down Trepi Street – escaping through ‘the eye of the needle’. Only a special handful of felons were able to find safe passage along this narrow alleyway and all of them went on to live very pious lives. Most ended up in the gallows.

Where can I find the Eye of the Needle?

Re-create the ‘final road’ that these condemned criminals would have taken by walking from the Old Town Square to Freedom Square, along Harju Street. You will see the Eye of the Needle on your right hand side.

5) The Old Town Pervert

After so much talk of Devils and executions, we will end on a note of humour. This may even be my favourite Tallinn legend of them all.

The building on the corner of Pikk and Hobusepea Street once housed a beautiful young woman and her husband. One evening, as the woman undressed, she noticed an old man sitting in the window opposite, holding a pair of ‘opera glasses’ and watching her. Disgusted, she threw on her clothes and ran downstairs.

To exact revenge, the husband hired the most skilful sculptor he could afford to craft a statue of the old man (complete with his infamous ‘opera glasses’) which he placed on top of his house. The next time the frisky old man came to his window he would be confronted by his own twin, cast in stone, staring back at him.

How can I find the statue of the Old Town Pervert? HeadHERE and look up